EP3315562B1 - Electroconductive liquid composition - Google Patents

Electroconductive liquid composition Download PDF

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Publication number
EP3315562B1
EP3315562B1 EP16816159.4A EP16816159A EP3315562B1 EP 3315562 B1 EP3315562 B1 EP 3315562B1 EP 16816159 A EP16816159 A EP 16816159A EP 3315562 B1 EP3315562 B1 EP 3315562B1
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EP
European Patent Office
Prior art keywords
liquid composition
conductive liquid
mass
conductive
composition according
Prior art date
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EP16816159.4A
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German (de)
English (en)
French (fr)
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EP3315562A1 (en
EP3315562A4 (en
Inventor
Yuka Niwayama
Miki Hosoda
Hiroyoshi SHINJYO
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Teikoku Printing Inks Manufacturing Co Ltd
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Teikoku Printing Inks Manufacturing Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/20—Conductive material dispersed in non-conductive organic material
    • H01B1/24—Conductive material dispersed in non-conductive organic material the conductive material comprising carbon-silicon compounds, carbon or silicon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/22—Tin compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/22—Tin compounds
    • C07F7/2224—Compounds having one or more tin-oxygen linkages
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4081—Mixtures of compounds of group C08G18/64 with other macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/58—Epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
    • C08G18/6415—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • C08K5/57—Organo-tin compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C08L101/06—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/52—Electrically conductive inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/24—Electrically-conducting paints
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/20—Conductive material dispersed in non-conductive organic material
    • H01B1/22—Conductive material dispersed in non-conductive organic material the conductive material comprising metals or alloys
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41F—PRINTING MACHINES OR PRESSES
    • B41F17/00—Printing apparatus or machines of special types or for particular purposes, not otherwise provided for
    • B41F17/001—Pad printing apparatus or machines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
    • C08F2500/02—Low molecular weight, e.g. <100,000 Da.
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/001—Conductive additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/002—Physical properties
    • C08K2201/005—Additives being defined by their particle size in general
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/02—Polyureas
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes

Definitions

  • the present invention relates in particular to a conductive liquid composition that can be applied for both flexible plastic film substrates and glass substrates, the conductive liquid composition being usable for antistatic purposes and for electromagnetic wave shields.
  • the invention further relates to a conductive liquid composition having an antistatic function and an electromagnetic wave shield function that exhibits a very excellent leveling property (surface smoothness) as a coated film even with a thin film thickness of about 8 to 10 ⁇ m, and also excellent resistance to rinsing with organic solvents such as MEK.
  • Conductive liquid compositions are used in the production of semiconductor packages and microelectronic devices and in assembly, for various purposes including antistatic functions, electromagnetic wave shield functions and anisotropic conductive adhesive functions (die mounting adhesives and the like).
  • the coating layers of the conductive liquid compositions are also becoming thinner, and for solid patterns with low thicknesses of about 5 to 10 ⁇ m and wide areas (for example, about 50 mm ⁇ 80 mm), it is becoming increasingly difficult to achieve uniform and highly smooth surfaces for the conductive liquid composition coating layers, which has resulted in the problem of variation in conductive functioning at the coating layer locations.
  • the surface smoothness of a coated film tends to be improved when the conductive liquid composition coating layer is a thick film of about not less than an extent from 15 to 25 ⁇ m, but this solution not only increases the amount of conductive liquid composition used and results in higher cost, but also interferes with the aforementioned decrease in thickness.
  • the performance required for conductive liquid compositions naturally includes the ability for a single type of conductive liquid composition to be used in common for plastic substrates including flexible sheets and the like and conventional glass, and a conductive function that ensures adequate performance for the purpose even with a low film thickness, as well as a high leveling property (surface smoothness) to exhibit a uniform conductive function without fine irregularities even with thin coated films, and the ability to adequately withstand rinsing with MEK and the like that are used for removal of trace contamination.
  • a conductive function that ensures adequate performance for the purpose even with a low film thickness, as well as a high leveling property (surface smoothness) to exhibit a uniform conductive function without fine irregularities even with thin coated films, and the ability to adequately withstand rinsing with MEK and the like that are used for removal of trace contamination.
  • Prior Patent Document 1 Japanese Unexamined Patent Application Publication No. 2015-230847 discloses metal covered particles with high conductivity and a conductive resin composition containing the metal covered particles, but it does not disclose technology relating to a conductive liquid composition that can be used in common for plastic substrates and glass substrates, nor does it disclose technology relating to formation of a coated film with a high degree of surface smoothness even as a thin-film, and able to adequately withstand organic solvent rinsing.
  • Prior Patent Document 2 Japanese Patent Public Inspection No. 2016-513143 discloses technology relating to a conductive ink composition that is satisfactory for flexible film substrates, but it does not disclose a technology allowing common use for glass substrates as well, or technology relating to the formation of a coated film with a high degree of surface smoothness even as a thin-film, and able to withstand organic solvent rinsing.
  • Prior Patent Document 3 Japanese Patent Public Inspection No. 2010-539650 discloses a conductive composition including a binder and filler particles with a silver plated core, the composition having a sheet resistivity of not more than about 0.100 ⁇ /sq./25 ⁇ m, but it does not disclose a technology allowing common use for both plastic substrates and glass substrates, or technology relating to the formation of a coated film with a high degree of surface smoothness even as a thin-film, and able to withstand organic solvent rinsing.
  • Prior Patent Document 4 Japanese Patent Public Inspection No. 2011-526309 discloses a conductive curable composition filled with a silver-coated flaky material, the disclosure also relating to the viscosity and thixotropic property of the composition. However, it does not disclose a technology allowing common use for both plastic substrates and glass substrates, nor does it disclose a technology relating to the formation of a coated film with a high degree of surface smoothness even as a thin-film, and able to withstand organic solvent rinsing.
  • WO 2014/112433 A1 discloses an electroconductive paste which comprises a thermoplastic resin, an electroconductive powder, an ion scavenger and an organic solvent, wherein the thermoplastic resin is polyurethane resin, has a molecular weight of 8000-60000, and a glass transition temperature of 60-100° C, and wherein the electroconductive powder comprises silver and the electroconductive paste further comprises 0.5-10 parts per wt. silica particles, and 0.1-5 parts per wt. carbon black with respect to 100 parts per wt. thermoplastic resin, electroconductive powder, and ion scavenger.
  • the present invention has been devised in light of the problems mentioned above, and as a technology that has no previous disclosure, it relates to a conductive liquid composition that can be used as a single type of conductive liquid composition for plastic substrates such as flexible sheets and films, and conventional glass, that has a conductive function exhibiting adequate performance for a given purpose even with a low film thickness, and also a high leveling property (surface smoothness) to exhibit a uniform conductive function without fine irregularities even with thin coated films, and that can form a coating layer with the ability to withstand rinsing with MEK used for removal of trace contamination, as well as an article having a coating layer of the conductive liquid composition and a method for producing the article.
  • the present invention relates to a conductive liquid composition
  • a conductive liquid composition comprising:
  • the conductive liquid composition of the invention it has become possible to obtain a conductive liquid composition that can be used as a single type of conductive liquid composition for plastic substrates including flexible sheets, and conventional glass substrates, that has an adequate electromagnetic wave shield function and antistatic function even with a low film thickness, and also a high leveling property (surface smoothness) even as a thin coated film, and can form a coating layer with the ability to adequately withstand rinsing with MEK used for removal of trace contamination, as well as an article having a coating layer of the conductive liquid composition and a method for producing the article.
  • the invention relates to a conductive liquid composition
  • a conductive liquid composition comprising:
  • the invention further relates to a conductive liquid composition wherein the viscosity of the conductive liquid composition is from 0.1 to 100 Pa ⁇ s when measured at 25 ⁇ 1°C by a BH-type rotating viscosimeter at 20 rpm/min.
  • the composition can be used to an ink for screen printing.
  • the invention further relates to a conductive liquid composition wherein the viscosity of the conductive liquid composition is from 1.0 to 60 Pa ⁇ s when measured at 25 ⁇ 1°C by a BH-type rotating viscosimeter at 20 rpm/min.
  • the composition can be used to an ink for pad printing.
  • the invention still further relates to a conductive liquid composition wherein the organometallic compound is a dibutyltin compound.
  • the invention still further relates to a conductive liquid composition wherein the coupling agent is a silane coupling agent.
  • the invention still further relates to a conductive liquid composition wherein the polyisocyanate is a block polyisocyanate having a curing reaction starting temperature of not less than 90°C.
  • the invention still further relates to a conductive liquid composition wherein the conductive liquid composition contains dimethylsilicon oil at from over O to 0.02 mass%.
  • the invention still further relates to an article having a coating layer of the conductive liquid composition.
  • the invention still further relates to a method for producing an article wherein an article is produced by coating the conductive liquid composition.
  • the conductive resin composition of the invention contains (A), for a binder resin, from 5 to 25 mass% of a hydroxyl-containing resin with a hydroxyl value from 3 to 100 and a weight-average molecular weight from 4000 to 20000.
  • the resin is one that, by addition of the curing agents, curing accelerators and coupling agents mentioned below, has excellent firm adhesion to a wide range of substrates including PET (polyester) resin substrates, PC (polycarbonate) resin substrates, polyimide resin substrates and polyolefin resin substrates, and flexibility that can adequately withstand bending and folding, and it is an essential component of the binder resin in the conductive liquid composition of the invention.
  • crosslinking reaction will not take place sufficiently even if the curing agent, curing accelerator and coupling agent described below are added, and the adhesiveness on substrates and resistance to rinsing with MEK will also be impaired, on the other hand, when it is more than 100, the crosslinking reaction will take place too rapidly, greatly shortening the pot life or extremely impairing the humidity resistance or alkali resistance.
  • Such resins include polyester resins, acrylic resins, epoxy resins, urethane resins and amic acid resins, any of which resins may be used alone or in combinations of two or more.
  • Polyester resins are most preferred among such hydroxyl-containing resins.
  • the weight-average molecular weight of the resin is from 4000 to 20000, preferably from 6000 to 18000 and more preferably from 7000 to 16000.
  • the adhesion onto different substrates will be inferior even if it is used in combination with a curing agent, curing accelerator and coupling agent, and the resistance to rinsing with MEK (methyl ethyl ketone) will also be inferior.
  • MEK methyl ethyl ketone
  • the weight-average molecular weight is more than 20000, the viscosity of the conductive liquid composition will be increased, impairing the surface smoothness or resulting in poor coating work efficiency.
  • the resin content may be from 5 to 25 mass%, preferably from 8 to 20 mass% and more preferably from 10 to 15 mass% with respect to the total amount of conductive resin composition.
  • the adhesion on different substrates may be impaired, or the resistance to rinsing with MEK may be impaired, or deterioration in the surface smoothness due to irregularities in the conducting material as described below may become apparent.
  • the resin content is more than 25 mass%, the viscosity of the conductive liquid composition will be increased, impairing the surface smoothness or resulting in poor coating work efficiency.
  • the conductive liquid composition of the invention contains (B), for a solvent, one or more solvents with boiling points of not less than 170°C selected from among isophorone, dibasic acid esters, 3-methoxy-3-methylbutanol, 3-methoxy-3-methylbutyl acetate, ethyleneglycol monobutyl ether acetate, coal tar naphtha with a boiling point of more than 170°C, diethyleneglycol monoethyl ether, diethyleneglycol monoethyl ether acetate, diethyleneglycol monobutyl ether, diethyleneglycol monobutyl ether acetate, triethyleneglycol monobutyl ether, triethyleneglycol monobutyl ether acetate, polyethyleneglycol dimethyl ether, tetraethyleneglycol dimethyl ether and polyethyleneglycol monomethyl ether, at not less than 70 mass% of the total solvent, but the content is preferably not less than 80 mass% and more preferably not
  • isophorone coal tar naphtha with a boiling point of more than 170°C
  • butylcellosolve acetate and dibasic acid esters e.g. dialkyl adipate ester-containing solvents
  • Dibasic acid esters are marketed, for example, under the trade name of FlexisolvDBE by Invista.
  • the leveling property may be impaired and it may not be possible to obtain a high level of surface smoothness for the conductive liquid composition.
  • drying of the conductive liquid composition on the screen plate will be more rapid and clogging of the screen plate will tend to occur.
  • the solvents other than the solvent with a boiling point of not less than 170°C contained in the conductive liquid composition of the invention but in order to reduce the azeotropic evaporation rate of the solvent with a boiling point of not less than 170°C and maintain a high level of surface smoothness, and to ensure mass production stability in screen printing coating, it is preferred to use a solvent with a boiling point of not less than 100°C, examples of such solvents including xylene, cyclohexanone, coal tar naphtha with a boiling point from 160°C to 170°C, mineral spirits with a boiling point from 150°C to 170°C, 1-methoxy-2-propanol, 1-methoxypropyl-2-acetate and diacetone alcohol.
  • the solvent of the invention only needs to contain not less than 70 mass% of a solvent with a boiling point of not less than 170°C of the total solvent, but in order to further stabilize the printing property when a conductive pattern including a fine pattern is to be obtained by screen printing, it is desirable for the boiling point of the solvent to be not less than 190°C.
  • the total amount of solvent with respect to the total amount of the conductive liquid composition of the invention is naturally the amount other than the other components, and it is preferably at least 10 mass% in order to satisfactorily ensure surface smoothness for the coated film.
  • the present invention contains (C), for a curing agent, a polyisocyanate at from 1.5 to 10.0 mass%, for crosslinking reaction with the binder resin to ensure firm adhesion with the substrate, and to improve the durability against rinsing with solvents such as MEK.
  • C for a curing agent, a polyisocyanate at from 1.5 to 10.0 mass%, for crosslinking reaction with the binder resin to ensure firm adhesion with the substrate, and to improve the durability against rinsing with solvents such as MEK.
  • polyisocyanates examples include polyisocyanates such as tolylene diisocyanate, xylene diisocyanate, isophorone diisocyanate and hexamethylene diisocyanate, and polyisocyanates of isophorone diisocyanate and hexamethylene diisocyanate are preferred in consideration of weather resistance, heat resistance and durability.
  • the polyisocyanate content is less than 1.5 mass%, it will be impossible to obtain a sufficiently crosslinked coating film and the adhesion or MEK rinsability will be inferior, while when it is more than 10.0 mass%, unreacted curing agent will remain and similarly the adhesion or MEK rinsability will be inferior.
  • the polyisocyanate is preferably a block polyisocyanate having a curing reaction starting temperature of not less than 90°C.
  • the pot life will usually be from about from several hours to ten or more hours.
  • the invention also contains, for a curing accelerator, (D) from 0.005 to 0.1 mass% of an organometallic compound, although the content is preferably from 0.01 to 0.05 mass% and more preferably from 0.01 to 0.03 mass%.
  • organometallic compounds for the curing accelerator include organic cobalt compounds, organic molybdenum compounds, organic tin compounds and organic titanium compounds, and organic tin compounds are satisfactory, dibutyltin compounds are especially satisfactory, and dibutyltin laurate is particularly suitable, and for compounds having excellent shelf life of the conductive liquid composition and significant curing acceleration with addition in very trace amounts.
  • the curing accelerator When the curing accelerator is present at less than 0.005 mass%, a reaction acceleration effect will not be obtained and adhesion defects may occur when the conductive liquid composition has been coated on a glass substrate and cured by heat drying at 150°C for 30 minutes, while the resistance to rinsing with MEK will also be impaired. On the other hand, when the curing accelerator is present at more than 0.1 mass%, curing of the conductive liquid composition will proceed too fast at ordinary temperature, and the pot life will be very short, at about from 1 to 2 hours.
  • the invention further relates to a conductive liquid composition which also contains as an adhesion reinforcing agent particularly for glass substrates, (E) a coupling agent at from 0.2 to 2.5 mass%, although the content is preferably from 0.3 to 2.0 mass% and more preferably from 0.4 to 2.0 mass%.
  • coupling agents may be given silane-based coupling agents, titanium-based coupling agents and phosphorus-based coupling agents.
  • Silane-based coupling agents are most satisfactory according to the experience of the present inventors. The reason for this is not completely understood but is conjectured to be that the presence of Si atoms in both the silane-based coupling agent and the glass substrate may contribute to their affinity.
  • the coupling agent content is less than 0.2 mass%, since the absolute amount will be reduced, the adhesion on glass substrates decreases. On the other hand, when it is more than 2.5 mass%, the excess coupling agent will presumably lead to inferior adhesion onto glass and reduced resistance to rinsing with MEK.
  • the conductive liquid composition of the invention has a surface resistivity from 1 to 1000 ⁇ /sq., and more preferably from 10 to 100 ⁇ /sq., when the thickness of the cured film of the conductive liquid composition is 8 ⁇ m.
  • G surface resistivity (also known as "sheet resistance”) of the conductive liquid composition of the invention is measured by forming a dry cured film of the conductive liquid composition to a thickness of 8 ⁇ m and a size of 50 mm ⁇ 80 mm, on a glass substrate or a flexible polyimide substrate, flexible PET substrate, and conducting measurement by the 4-terminal method is based on JIS K 7194. For example, it may be measured with a "K-705RS Four-point probe meter", in which the measurement adopts the direct current four-point probe method with units of ⁇ /sq.
  • the surface resistivity range of the conductive liquid composition of the invention is limited to from 1 to 1000 ⁇ /sq. when the coating layer of the conductive liquid composition has been formed to a thickness of 8 ⁇ m, but even in the case of a product with the conductive liquid composition coated to another thickness, for example, such as 10 ⁇ m or 13 ⁇ m, the used conductive liquid composition belongs to the scope of the invention as long as the surface resistivity is from 1 to 1000 ⁇ /sq. when the conductive liquid composition used has been formed to a coated film of 8 ⁇ m, and the other conditions of the invention are simultaneously satisfied.
  • the conductive liquid composition of the invention further contains (F), as conducting materials: (f1) from 2.0 to 10.0 mass% of graphite, (f2) from 5.0 to 15.0 mass% of conductive carbon black and (f3) from 20.0 to 50.0 mass% of silica particles having a mean particle size from 1.0 to 7.0 ⁇ m and surface-coated with silver, the more preferred ranges being (f1) from 3.0 to 7.0 mass% of graphite, (f2) from 7.0 to 12.0 mass% of conductive carbon black and (f3) from 30.0 to 45.0 mass% of silica particles having a mean particle size from 1.5 to 6.0 ⁇ m and surface-coated with silver.
  • (F) as conducting materials: (f1) from 2.0 to 10.0 mass% of graphite, (f2) from 5.0 to 15.0 mass% of conductive carbon black and (f3) from 20.0 to 50.0 mass% of silica particles having a mean particle size from 1.0 to 7.0 ⁇ m and surface-coated with silver, the more preferred ranges being (f1)
  • (f1) graphite used preferably has a mean particle size of not more than about 8 ⁇ m, since the conductive resin composition of the invention may be used even in the case of a thin-film of about 8 ⁇ m.
  • a primary particle size is generally from 10 to 100 nm and a secondary particle structure is a structure with primary particles connected in chains, a longer structure with associated has more excellent conductive function.
  • the average length of the structure is preferably about from 20 to 60 ⁇ m in order to ensure a balance between conductive function, dispersibility and surface smoothness.
  • the conductive liquid composition coating layer When the content of the conductive carbon black is less than 5.0 mass%, the conductive liquid composition coating layer will be less likely to have a high degree of surface smoothness, presumably for the reasons described in paragraph [0045] below, on the other hand, when it is more than 15.0 mass%, the dispersion time will be undesirably lengthened.
  • the mean particle sizes must be less than 8 ⁇ m, or from 1.0 to 7.0 ⁇ m, and are more preferably from 1.5 to 6.0 ⁇ m.
  • the abrasion resistance and MEK rinsing resistance of the conductive liquid composition coating layer will be inferior, and the viscosity of the conductive liquid composition will also be too high, thus hampering the coating operation.
  • the content is less than 20.0 mass%, of course, obtaining sufficient conductive function becomes difficult and such a state is undesirable.
  • (f1) graphite as the conducting material has a suitable conductive function, but because of its high specific gravity, when used alone, problem of easily precipitating in the conductive liquid composition may not be avoided.
  • (f2) conductive carbon black does not have a high conductive function
  • the present inventors have found that it has a property of exhibiting high surface smoothness in the conductive liquid composition of the invention.
  • the reason of the smoothness is not certain, and it may be presumed that by addition of the specific conductive carbon black as is described in paragraph [0043], the configurations of the other included filler particles and the resin molecules are controlled during film formation with the conductive liquid composition, resulting to surprisingly satisfactory surface smoothness.
  • (f3) silver-coated silica particles used for the invention are preferably ones formed by electroless plating and having a mean particle size from 1.0 to 7.0 ⁇ m.
  • the silver-coated silica is highly superior for adjustment of electric resistivity, but when its content is high, the abrasion resistance and MEK rinsing resistance will be inferior and the viscosity of the conductive liquid composition will also be too high, thus hampering the coating operation. Naturally, when the content is reduced, on the other hand, it will not be possible to obtain an adequate conductive function.
  • the mean particle size of the (f3) silver-coated silica particles is less than 1.0 ⁇ m, the dispersibility will tend to be impaired and the conductive function will be slightly reduced. On the other hand, when it is more than 7.0 ⁇ m, coating the conductive liquid composition to a film thickness of 8 ⁇ m may adversely affect the surface smoothness.
  • the present inventors have discovered that in order to obtain a conductive coated film satisfying the conductive function specified by the invention (a surface resistivity from 1 to 1000 ⁇ /sq.), and having a high level of surface smoothness even as a thin-film of 8 ⁇ m while also being able to withstand rinsing with MEK, it is necessary for the conductive liquid composition to contain, as conducting materials, (f1) from 2.0 to 10.0 mass% of graphite, (f2) from 5.0 to 15.0 mass% of conductive carbon black and (f3) from 20.0 to 50.0 mass% of silica particles surface-coated with silver, with a mean particle size from 1.0 to 7.0 ⁇ m, and the invention has been completed upon said discovery.
  • the invention can be suitably used as an ink for screen printing.
  • the invention can be suitably used to an ink for pad printing.
  • the viscosity is less than 1.0 Pa ⁇ s, the ink transfer volume onto the pad will be reduced and it will be difficult to accomplish satisfactory pad printing, on the other hand, when it is more than 60 Pa ⁇ s, stringing of the ink between the plate and the pad will be more likely to occur and it will be difficult to obtain the desired printed image.
  • the method for coating the conductive liquid composition of the invention is not limited to screen printing and pad printing methods, and coating may instead be carried out by, for example, spray coating, dispenser coating, gravure printing or flexographic printing, if the viscosity has been adjusted to about from 0.1 to 1.0 Pa ⁇ s.
  • the present invention may also contain a dimethylsilicon oil at from over 0 to 0.02 mass%, in order to minimize formation of air bubbles during high-speed coating or high-speed printing of the conductive liquid composition.
  • the present invention further provides articles with the conductive liquid composition of the invention coated on a flexible thermoplastic resin film or sheet substrate such as PET, PC, polypropylene, polyethylene or polyimide, or a glass substrate.
  • a flexible thermoplastic resin film or sheet substrate such as PET, PC, polypropylene, polyethylene or polyimide, or a glass substrate.
  • the present invention still further provides a method for producing an article wherein the article is produced by coating the conductive liquid composition of the invention on a flexible thermoplastic resin film or sheet substrate such as PET, PC, polypropylene, polyethylene or polyimide, or a glass substrate.
  • a flexible thermoplastic resin film or sheet substrate such as PET, PC, polypropylene, polyethylene or polyimide, or a glass substrate.
  • the conductive liquid compositions of the examples and comparative examples in Table 1 were produced by precisely measuring out the materials in the amounts listed in the table into a production vessel, subsequently stirring with a propeller rotating stirrer until the material became thoroughly uniform, and then forming a dispersion by 2 passes with a triple roll mill.
  • the coated film was formed by screen printing (coating area: 80 mm ⁇ 50 mm rectangle, coated film thickness after drying curing: 8 ⁇ m), and dry curing was carried out at 150°C for 30 minutes.
  • the coated film on a flexible polyimide substrate with a thickness of 125 ⁇ m was subjected to a crosscut cellophane tape peeling test on a grid with 100 pieces of 1 mm-squares (hereunder referred to simply as “grid peeling test”), and to a scratch peeling test with the fingernail (hereunder referred to simply as “fingernail peeling test,” with an evaluation of "G" to be satisfactory.
  • the coated film on a 2 mm-thick glass substrate was subjected to a grid peeling test and a fingernail peeling test, with an evaluation of "G" being considered satisfactory.
  • the coated film on a flexible polyimide substrate with a thickness of 125 ⁇ m was subjected to 180° folding three times, together with a polyimide substrate, and the outer appearance of the coated film was observed while changes in the electric resistivity were measured, with an evaluation of "G" being considered satisfactory.
  • the surface roughness of the coated film on a flexible polyimide substrate with a thickness of 125 ⁇ m was measured with a surface roughness measuring instrument SV-600 by Mitsutoyo Corporation.
  • the coated film on a flexible polyimide substrate with a thickness of 125 ⁇ m was immersed for 1 hour in an MEK solution, and then the outer appearance of the coated film was observed while changes in the electric resistivity were measured, with an evaluation of "G" to be satisfactory.
  • the coated film on a flexible polyimide substrate with a thickness of 125 ⁇ m was subjected to potential resistivity measurement by a K-705RS four-point probe meter of Kyowa Riken Co., Ltd. using the direct-current four-point probe method, with an evaluation of VG or G to be satisfactory.
  • Example 5 when the conductive liquid resin composition of Example 5 was used to form a coating layer with a dry cured film thickness of 8 ⁇ m on a flexible imide film substrate by pad printing, it was possible to manufacture articles simultaneously satisfying the required performance aspects mentioned in [0056], and having a satisfactory electromagnetic wave shield functions and antistatic functions, similar to Example 5.
EP16816159.4A 2016-09-02 2016-09-02 Electroconductive liquid composition Active EP3315562B1 (en)

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JP2021102700A (ja) * 2019-12-25 2021-07-15 Dic株式会社 コーティング剤、積層体、成型体及び包装材
CN112867285B (zh) * 2020-12-29 2022-10-04 深圳市贝加电子材料有限公司 一种导电石墨孔金属化溶液及其制备方法和应用
CN115558378A (zh) * 2022-10-31 2023-01-03 上海席亚高分子材料有限公司 一种超薄涂层导电涂料及其制备方法

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CN107636095B (zh) 2019-04-23
PH12017500129B1 (en) 2017-05-29
PH12017500129A1 (en) 2017-05-29
TWI596172B (zh) 2017-08-21
CN107636095A (zh) 2018-01-26
KR101766629B1 (ko) 2017-08-08
WO2018042635A1 (ja) 2018-03-08
US10081735B1 (en) 2018-09-25
TW201811933A (zh) 2018-04-01
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IL251346A (en) 2017-07-31
EP3315562A4 (en) 2018-11-21

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